Dimethylamine → HCID 53992192, compound

HRID 894088Notes

Reaction equation

HRID 894088 reaction equation
[CH3:1][N:2]([CH3:5])[CH:3]=O.P(Cl)(Cl)([Cl:8])=O.C[O:12][CH:13](OC)[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19](Cl)=[CH:18][CH:17]=1.[OH-].[Na+].CNC>O.C(Cl)(Cl)Cl>[Cl:8][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[O:15][C:14](=[CH:3][N:2]([CH3:5])[CH3:1])[CH:13]=[O:12]

Participants

8

Reactant 5

HCID 674DimethylamineHCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 15510276HCID 15510276, compound

Product 1

HCID 53992192HCID 53992192, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

Dimethylformamide (109.5 g., 1.5 moles) was cooled in an ice-water bath. Phosphorus oxychloride (229.5 g., 1.5 moles) was added dropwise over 1.5 hours and the reaction mixture then allowed to stir for 45 minutes at room temperature. Chloroform (300 ml.) was added and then 4-chlorophenoxyacetaldehyde dimethylacetal (122 g., 0.5 moles) and the mixture refluxed for approximately 16 hours. The reaction was cooled to room temperature and added slowly to approximately 300 ml. of chloroform mixed with ice and water while maintaining the pH approximately 10 with sodium hydroxide. Aqueous 40% dimethylamine (400 ml.) was added, the organic layer separated and the aqueous extracted with additional chloroform. The chloroform extracts were combined, dried over anhydrous sodium sulfate, concentrated to a semisolid, and crystalline product recovered by trituration with isopropyl ether (95 g., Rf 0.25 on thin layer chromatography on silica gel with ethyl acetate as eluant).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. additionadded slowly to approximately 300 ml
  3. customthe organic layer separated
  4. extractionthe aqueous extracted with additional chloroform
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated to a semisolid, and crystalline product
  7. customrecovered by trituration with isopropyl ether (95 g., Rf 0.25 on thin layer chromatography on silica gel with ethyl acetate as eluant)

Sources & evidence

ORD record
ord-a5222482f86d4f15bb0da03970691a1c
Source dataset
uspto-grants-1981_08
Patent number
US04282242

Reaction notes

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